TRANS-2-HEXEN-1-OL

Description

2-Hexen-l-ol has a powerful, fruity, green, wine-like, leafy odor and a sweet, fruity flavor important to strawberry and orange juice. The ds-form can be prepared by hydrogenation of ds-2-hexenol, using an aqueous suspension of colloidal palladium; from cis- 4-chloro-2-butenol and magnesium ethyl bromide; the commercial product is a mixture of the cis- and trans-isomers and can be prepared from propyl vinyl carbinol by heating with aluminum oxide.

Chemical properties

2-Hexen-1-ol has a powerful, fruity-green odor, with a sweet, fruity flavor important to strawberry and orange juice

Occurrence

Reported found as a constituent of fresh raspberry aroma; also identified in Valencia orange juice and apple aroma, probably occurring as an ester. Also reported found in raw and cooked asparagus, cooked potato, cooked beef, hop oil, brandy, beer, white wine, roasted peanut, soybean, olive, prune, prickly pear, malt, kiwifruit, loquat, quince, apple, peach, strawberry, tamarind, tomato and tea

The Uses of TRANS-2-HEXEN-1-OL

Trans-2-hexen-1-ol's use in perfumes is somewhat limited. Lavender and Lavandin oil compositions may benefit from the topnote created with this alcohol, and certain floral bouquets can be improved with pleasantly green, sweet and natural notes from the subject material. It finds increasing use in artificial Geranium oils.
In flavors, traces are used in fruit complexes, and it is a common ingredient in artificial Strawberry. It adds freshness to Mint compositions, and it is often used to reconstitute the flavor in Orange juice, whose flavor suflers severely during the processing.

Preparation

The cis-form can be prepared by hydrogenation of cis-2-hexenol, using an aqueous suspension of colloidal palladium; from cis-4-chloro-2-butenol and magnesium ethyl bromide; the commercial product is a mixture of the cis- and trans-isomers and can be prepared from propyl vinyl carbinol by heating with aluminum oxide.

Definition

ChEBI: 2-hexen-1-ol is a primary allylic alcohol that is 2-hexene in which a hydrogen at position 1 has been replaced by a hydroxy group. It has a role as a plant metabolite. It is an alkenyl alcohol and a primary allylic alcohol.

Aroma threshold values

Aroma characteristics at 1.0%: fresh, fatty green, tomato vegetative, with leafy, green fruity and herbal nuances.

Taste threshold values

Taste characteristics at 5 ppm: fresh, leafy green, slightly fatty with grassy, fruity and juicy nuances, tomato and celery nuances.